Characterization of 14,15-epoxyeicosatrienoyl-sulfonamides as 14,15-epoxyeicosatrienoic acid agonists: Use for studies of metabolism and ligand binding

Journal of Pharmacology and Experimental Therapeutics

Volumn 321, Issue 3, 2007, Pages 1023-1031

  Yang, Wenqi ^a   Holmes, Blythe B ^a   Gopal, V Raj ^b   Kishore, R V Krishna ^b   Sangras, Bhavani ^b   Yi, Xiu Yu ^a   Falck, J R ^b   Campbell, William B ^a  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

^b UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

14,15 EPOXYEICOSA 5 ENOYLMETHYLSULFONAMIDE; 14,15 EPOXYEICOSATRIENOIC ACID AFFECTING AGENT; 14,15 EPOXYEICOSATRIENOYL BENZOYLDIHYDROCINNAMIDE SULFONAMIDE; 14,15 EPOXYEICOSATRIENOYL BIOTINSULFONAMIDE; 14,15 EPOXYEICOSATRIENOYL PHENYLIODOSULFONAMIDE; AGENTS INTERACTING WITH TRANSMITTER, HORMONE OR DRUG RECEPTORS; ARACHIDONIC ACID; CALCIUM ACTIVATED POTASSIUM CHANNEL; EPOXIDE HYDROLASE; EPOXYICOSATRIENOIC ACID; IBERIOTOXIN; LIGAND; SULFONAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BLOOD VESSEL TONE; CELL STRAIN U937; CONTROLLED STUDY; CORONARY ARTERY; COW; DRUG INHIBITION; HUMAN; HUMAN CELL; HYPERPOLARIZATION; LIGAND BINDING; METABOLISM; NONHUMAN; PRIORITY JOURNAL;

15-HYDROXY-11 ALPHA,9 ALPHA-(EPOXYMETHANO)PROSTA-5,13-DIENOIC ACID; 8,11,14-EICOSATRIENOIC ACID; ANIMALS; BINDING, COMPETITIVE; CATTLE; CELL MEMBRANE; CORONARY VESSELS; HUMANS; LARGE-CONDUCTANCE CALCIUM-ACTIVATED POTASSIUM CHANNELS; LIGANDS; MOLECULAR STRUCTURE; PEPTIDES; SUBCELLULAR FRACTIONS; SULFONAMIDES; U937 CELLS; VASODILATION; VASODILATOR AGENTS;

EID: 34248570494     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.107.119651     Document Type: Article

References (39)

1. Backes BJ and Ellman JA (1994) Carbon-carbon bond-forming methods on solid support: utilization of Kenner's "safety-catch" linker. J Am Chem Soc 116:11171-11172.
2. Campbell WB, Gebremedhin D, Pratt PF, and Harder DR (1996) Identification of epoxyeicosatrienoic acids as endothelium-derived hyperpolarizing factors. Circ Res 78:415-423.
3. Capdevila J, Parkhill L, Chacos N, Okita R, Masters BS, and Estabrook RW (1981) The oxidative metabolism of arachidonic acid by purified cytochromes P-450. Biochem Biophys Res Commun 101:1357-1363.
4. Corey EJ, Niwa H, and Falck JR (1979) Selective epoxidation of eicosa-cis-5,8,11,14-tetraenoic (arachidonic) acid and eicosa-cis-8,11,14- trienoic acid. J Am Chem Soc 101:586-587.
5. Cowart LA, Wei S, Hsu MH, Johnson EF, Krishna MU, Falck JR, and Capdevila JH (2002) The CYP4A isoforms hydroxylate epoxyeicosatrienoic acids to form high affinity peroxisome proliferator-activated receptor ligands. J Biol Chem 277:35105-35112.
6. Falck JR, Krishna UM, Reddy YK, Kumar PS, Reddy KM, Hittner SB, Deeter C, Sharma KK, Gauthier KM, and Campbell WB (2003a) Comparison of vasodilatory properties of 14,15-EET analogs: structural requirements for dilation. Am J Physiol 284:H337-H349.
7. Falck JR, Reddy LM, Reddy YK, Bondlela M, Krishna UM, Ji Y, Sun J, and Liao JK (2003b) 11,12-epoxyeicosatrienoic acid (11,12-EET): structural determinants for inhibition of TNF-alpha-induced VCAM-1 expression. Bioorg Med Chem Lett 13:4011-4014.
8. Fisslthaler B, Popp R, Kiss L, Potente M, Harder DR, Fleming I, and Busse R (1999) Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature (Lond) 401:493-497.
9. Fukao M, Mason HS, Kenyon JL, Horowitz B, and Keef KD (2001) Regulation of BK(Ca) channels expressed in human embryonic kidney 293 cells by epoxyeicosatrienoic acid. Mol Pharmacol 59:16-23.
10. Fulton D, Mahboubi K, McGiff JC, and Quilley J (1995) Cytochrome P450-dependent effects of bradykinin in the rat heart. Br J Pharmacol 114:99-102.
11. Gauthier KM, Edwards EM, Falck JR, Reddy DS, and Campbell WB (2005) 14,15-epoxyeicosatrienoic acid represents a transferable endothelium-dependent relaxing factor in bovine coronary arteries. Hypertension 45:666-671.
12. Gauthier KM, Falck JR, Reddy LM, and Campbell WB (2004) 14,15-EET analogs: characterization of structural requirements for agonist and antagonist activity in bovine coronary arteries. Pharmacol Res 49:515-524.
13. Gauthier KM, Jagadeesh SG, Falck JR, and Campbell WB (2003) 14,15-epoxyeicosa-5(Z)-enoic-mSI: a 14,15- and 5,6-EET antagonist in bovine coronary arteries. Hypertension 42:555-561.
14. Huang A, Sun D, Jacobson A, Carroll MA, Falck JR, and Kaley G (2005) Epoxyeicosatrienoic acids are released to mediate shear stress-dependent hyperpolarization of arteriolar smooth muscle. Circ Res 96:376-383.
15. Imig JD, Falck JR, Wei S, and Capdevila JH (2001) Epoxygenase metabolites contribute to nitric oxide-independent afferent arteriolar vasodilation in response to bradykinin. J Vasc Res 38:247-255.
16. Kanai N, Lu R, Satriano JA, Bao Y, Wolkoff AW, and Schuster VL (1995) Identification and characterization of a prostaglandin transporter. Science (Wash DC) 268:866-869.
17. Kort Md, Luijendijk J, Marel GAvd, and Boom JHv (2000) Synthesis of photoaffinity derivatives of adenophostin A. Eur J Org Chem 2000:3085-3092.
18. Kozak W, Kluger MJ, Kozak A, Wachulec M, and Dokladny K (2000) Role of cytochrome P-450 in endogenous antipyresis. Am J Physiol 279:R455-R460.
19. Krischer SM, Eisenmann M, and Mueller MJ (1998) Transport of arachidonic acid across the neutrophil plasma membrane via a protein-facilitated mechanism. Biochemistry 37:12884-12891.
20. Leier I, Jedlitschky G, Buchholz U, Cole SP, Deeley RG, and Keppler D (1994) The MRP gene encodes an ATP-dependent export pump for leukotriene C4 and structurally related conjugates. J Biol Chem 269:27807-27810.
21. + channels in coronary smooth muscle through a guanine nucleotide binding protein. Circ Res 80:877-884.
22. Li PL, Chen CL, Bortell R, and Campbell WB (1999) 11,12- Epoxyeicosatrienoic acid stimulates endogenous mono-ADP-ribosylation in bovine coronary arterial smooth muscle. Circ Res 85:349-356.
23. Michaelis UR and Fleming I (2006) From endothelium-derived hyperpolarizing factor (EDHF) to angiogenesis: epoxyeicosatrienoic acids (EETs) and cell signaling. Pharmacol Ther 111:584-595.
24. Morisseau C, Goodrow MH, Newman JW, Wheelock CE, Dowdy DL, and Hammock BD (2002) Structural refinement of inhibitors of urea-based soluble epoxide hydrolases. Biochem Pharmacol 63:1599-1608.
25. Nithipatikom K, Grall AJ, Holmes BB, Harder DR, Falck JR, and Campbell WB (2001) Liquid chromatographic-electrospray ionization-mass spectrometric analysis of cytochrome P450 metabolites of arachidonic acid. Anal Biochem 298:327-336.
26. Nithipatikom K, Moore JM, Isbell MA, Falck JR, and Gross GJ (2006) Epoxyeicosatrienoic acids in cardioprotection: ischemic versus reperfusion injury. Am J Physiol 291:H537-H542.
27. Node K, Huo Y, Ruan X, Yang B, Spiecker M, Ley K, Zeldin DC, and Liao JK (1999) Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science (Wash DC) 285:1276-1279.
28. Node K, Ruan XL, Dai J, Yang SX, Graham L, Zeldin DC, and Liao JK (2001) Activation of Galpha s mediates induction of tissue-type plasminogen activator gene transcription by epoxyeicosatrienoic acids. J Biol Chem 276:15983-15989.
29. Pinto A, Abraham NG, and Mullane KM (1987) Arachidonic acid-induced endothelial-dependent relaxations of canine coronary arteries: contribution of a cytochrome P-450-dependent pathway. J Pharmacol Exp Ther 240:856-863.
30. Rosolowsky M and Campbell WB (1993) Role of PGI2 and epoxyeicosatrienoic acids in relaxation of bovine coronary arteries to arachidonic acid. Am J Physiol 264:H327-H335.
31. Rosolowsky M and Campbell WB (1996) Synthesis of hydroxyeicosatetraenoic (HETEs) and epoxyeicosatrienoic acids (EETs) by cultured bovine coronary artery endothelial cells. Biochim Biophys Acta 1299:267-277.
32. + channels and p42/p44 MAPK pathway. Circ Res 95:506-514.
33. Snyder GD, Krishna UM, Falck JR, and Spector AA (2002) Evidence for a membrane site of action for 14,15-EET on expression of aromatase in vascular smooth muscle. Am J Physiol 283:H1936-H1942.
34. Spearman ME, Prough RA, Estabrook RW, Falck JR, Manna S, Leibman KC, Murphy RC, and Capdevila J (1985) Novel glutathione conjugates formed from epoxyeicosatrienoic acids (EETs). Arch Biochem Biophys 242:225-230.
35. Spector AA, Fang X, Snyder GD, and Weintraub NL (2004) Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function. Prog Lipid Res 43:55-90.
36. Wong PY, Lai PS, and Falck JR (2000) Mechanism and signal transduction of 14 (R), 15 (S)-epoxyeicosatrienoic acid (14,15-EET) binding in guinea pig monocytes. Prostaglandins Other Lipid Mediat 62:321-333.
37. Wong PY, Lai PS, Shen SY, Belosludtsev YY, and Falck JR (1997) Post-receptor signal transduction and regulation of 14(R),15(S)- epoxyeicosatrienoic acid (14,15-EET) binding in U-937 cells. J Lipid Mediat Cell Signal 16:155-169.
38. Wong PY, Lin KT, Yan YT, Ahern D, Iles J, Shen SY, Bhatt RK, and Falck JR (1993) 14(R),15(S)-epoxyeicosatrienoic acid (14(R), 15(S)-EET) receptor in guinea pig mononuclear cell membranes. J Lipid Mediat 6:199-208.
39. Yang W, Gauthier KM, Reddy LM, Sangras B, Sharma KK, Nithipatikom K, Falck JR, and Campbell WB (2005) Stable 5,6-epoxyeicosatrienoic acid analog relaxes coronary arteries through potassium channel activation. Hypertension 45:681-686.